


Long Cool Woman

by kazosa



Category: Supernatural
Genre: Angst, F/M, Fluff, supernatural fan fiction
Language: English
Status: Completed
Published: 2018-07-23
Updated: 2018-07-23
Packaged: 2019-06-15 07:51:53
Rating: Not Rated
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 3,672
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/15408411
Author URL: https://archiveofourown.org/users/kazosa/pseuds/kazosa
Summary: Dean and the reader have a past. They were separated by circumstances beyond their control (so the kids thought). After a chance meeting years later, they begin talking…





	Long Cool Woman

Summary: Dean and the reader have a past. They were separated by circumstances beyond their control (so the kids thought). After a chance meeting years later, they begin talking…

A/N: I haven’t written in a few months. I found this in my notebooks and transcribed it. It was supposed to be part of a much larger story, but this was what I thought was the best part. Sorry if it’s crap. Yeay if it’s not!

* * *

**August 29, 1999**

    “You be careful out there,” Dean said. The sun was bright and just catching the side of his face, making his green eyes look even brighter than usual. “Monsters I get, it’s people that scare me.”

    Dean was wearing a dark green button-down shirt with a black t-shirt underneath, his jeans were dark and baggy, almost hiding his boots. His shirt was unbuttoned and the open ends of it lifted on the wind.

    You reached out and grabbed one end of his shirt, “I’ll be careful if you do.”

    Dean had made sure he gave you the best send-off he could, and it had been the best weekend of your life. You liked Dean, a lot, even when he kept putting his foot in his mouth. When he wasn’t trying to impress you, he was very sweet and you liked him much more. He’d driven you to the bus station so you could travel on for further military training, but you’d had to tell him that you were going to San Diego to ship out.

    “Deal,” he said, and gave you a hug and a quick kiss on the cheek. “Visit Bobby when you can, okay? For some reason, he likes you.”

    You saw through his façade, you always did.

    “I’ll do that and make sure he calls you, too, so we can all catch up,” you put your hand on his arm. “I’ll miss you, Dean.”

    The emotion was bubbling up inside you and you weren’t sure how much longer you could hold it back. You loved Dean Winchester and you had to walk away from him. He was born into a hunter family and you were going into special ops training, neither of which was a profession that worked well for relationships. If he said anything else to you, you weren’t sure you’d be able to go on to complete your training. You flashed him a quick smile and walked quickly away. The last thing you wanted was for him to see you crying. You were scared to go to your training, you were scared to leave him… You forced yourself to not look back. Getting on the bus, you took a seat and let it all out.

    Dean watched you walk away, fighting the lump that had formed in his throat. He took a deep breath and rubbed the palms of his hands on his jeans, desperately trying to get a good breath of air in. She’d practically run away, and, mercifully, she hadn’t turned back. He wiped his cheeks when the bus finally pulled away. The tightness in his throat eased a little and he slowly went back to the Impala. He really hoped she would call.

[Originally posted by luv4jensen](https://tmblr.co/ZrEDYe2QO6gPb)

**June 2012**

    Dean needed to blow off some steam. Sam went back to the hotel already, but Dean knew he wouldn’t be able to settle down for sleep. He needed to blow off some steam. Finding a bar that was near-by had worked out well. He didn’t care that he was still in his FBI suit, sometimes that worked well for him. The place he’d found had music playing and tons of people inside. Taking the first open barstool he found, he sat down and noticed there was a pool table near the back wall, opposite of where he sat.

    “What can I get ya?” the bartender asked.

    “Beer, whatever you have is fine,” he answered, scanning the rest of the bar.

    It looked like any other bar he’d ever been to, but slightly nicer. It looked nicer because of the wood and brass finishes as well as the stained glass that adorned the windows and doors. His eyes went back to the pool table and the crowd that was gathered around it. There was a small group of men standing around the table, seeming to Dean like they were trying to get with the woman that was, clearly, running the table. The guy se was playing was standing at the end of the table, arms crossed. To Dean, he looked like he hadn’t planned on having a woman beat him.

    The woman caught his attention just for the fact that she was running the table. She had on skin-tight, worn out jeans, black tank top, and old boots. Her hair was pulled back into a ponytail, just catching a glimpse of a chain around her neck.

    The bartender came back with a napkin and a beer with a perfect head.

    “Hey,” Dean got the bartender’s attention, “Do you know her, she a regular?”

    “Uh,” the bartender looked over his shoulder, “yeah,” he hedged, “she’s here often enough.”

    “Catch a name?” Dean hoped.

    The bartender stopped to eye Dean carefully, as though he were sizing him up.

    “(Y|L|N), but don’t tell her I told you,” he said and walked away to attend his other customers.

    Dean couldn’t speak. He couldn’t believe his ears. He stared at the woman, watching every move for some hint or confirmation of her identity. He took his glass to the jukebox. His heart pounded as he looked over the music selection. Every song he saw was a good one and reminded him of his time with (Y|N) and the music they would listen to when they would sneak off in his Impala.

    He pressed the button for the song he wanted and hit the “play my song next” button. Making his way back to his spot at the bar, he waited for his song to play, keeping a close eye on the woman.

    The first few bars of the Hollies “Long Cool Woman (In a Black Dress)” began to play and the woman turned to the bar and called out “Crank it!” She turned to the jukebox but went back to the table and sunk the 8 ball, winning the game. Exchanging money with her victims, she went to the bar.

    It had been a long time since you’d heard that song, years, at the very least. Always one of your favorites, you couldn’t help but call out to your bartender to turn it up loud. When you were still running missions, it would be one of the songs you would play when you and your crew would wind down. You’d broken your leg on a training jump that had gone poorly. You made a complete recovery, but you never were as fast as you had once been. When the lives of civilians and your crew were at stake, you just wouldn’t risk it.

    “Here you go, birthday girl,” your bartender, Henry handed you a drink.

    You looked up at him from your spot at the end of the bar, a questioning look on your face.

    “Guy in the suit said he owed you one,” Henry hooked a thumb in the direction of Suit Guy. “Is it really your birthday? In all the years I’ve known you, I don’t think I ever really knew what day it was.”

    “It’s not something I really like to think about. Stuff tends to happen on my birthday,” and it had all started on your 20th birthday when you left Dean to start a whole new life. It had been like the universe was telling you you had made a mistake. You looked down the length of the bar and saw Suit Guy watching you intently.

    “Holy shit,” you muttered.

    Henry, not knowing if it was shock or fear that made you react that way, “Need me to kick him out?”

    You were trying to get your legs under you to go talk to the man, see if he was real.

    “Nah, Henry,” you said, “He’s an old…friend.”

    Your relationship never really had the chance to go anywhere. He needed to hunt with his dad and you needed to be your own person, find your own way. Time had gotten away from you and months had turned into years.

    You took a gulp of your drink and made your way to the end of the bar. He played it cool, making casual eye contact with you the whole way. The last strains of “Long Cool Woman” played and the boy you had known turned to you just as you leaned on the bar near him.

    “Winchester,” you said.

    “(Y|L|N),” he responded.

     “You played my song.”

     Dean knew you liked that song. He also picked it because it reminded him of her. Her life of secrets, her long, sexy legs…

     “Yeah, thought it might get your attention,” he answered.

    You reached out, touching his arm. He was real. No tricks this time. In one quick move, she was in his arms being crushed to his body. After what Gabriel had done, you didn’t know if you could believe your eyes anymore. When he let loose his hold enough for you to lean back, you could feel the tears well up in your eyes but managed a smile when you saw his handsome face again. He’d actually gotten better looking, the jerk.

    Thankfully, you hadn’t told Gabriel everything about yourself and Dean. Gabriel knew that you’d had feelings for the elder Winchester, and you’d thought he was trying to help you move on. That hadn’t been the case and he’d put both Sam and Dean in a time-loop and done terrible things to them. You found out about what Gabriel had done after the fact, and you had told him exactly where he could go.

    The last days you and Dean were together, you kept those to yourself. It was a special time for the two of you. Bobby seemed to always be around, or Sam, and it was never just the two of you.

    “Tell me where we went on our last day together, our last good day,” you asked, wanting so desperately to believe.

    He didn’t even have to ask (Y|N) to know that something bad had happened while you were away. He wanted to know what, or who, it was that made you look so sad and disbelieving. He could only guess at this point.

    “We went to the Santa Monica Pier. Rode all the rides, ate all the food. Spent the whole day there, it was great,” he said, leaving off the end when they went back to the hotel.

    Finally, you had a real smile for him, “I’ve missed you.” You kissed him quickly and hugged him tight.

    Still holding you tightly to him, he spoke into your ear, “Let’s go someplace quiet, get caught up.”

    You nodded against his cheek, your eyes still tightly closed. After a few moments, he let go of you long enough to settle your tab and head outside to the parking lot and his car.

    “Oh my God, you have your dad’s car,” you said, admiring the fine cut of the Impala. “She looks a little different, though.”

    He went to the passenger side to open the door for you.

    “I had to rebuild her. Lots happened since I saw you last,” the slight tone in his voice was hard to miss.

    You got in the front seat and let him close the door for you. Once he was in the driver’s seat, you continued the conversation.

    “Well, you did a hell of a job, she still looks great,” you told him. “Where did you want to go?”

    “I…I don’t even know. Do you even live here? Hotel?” he asked.

    You knew he was asking if you were in from out of town, but you couldn’t hide the smirk.

    “Think we can just pick up where we left off, Winchester?” you asked. It had been a really great weekend all those years ago. Getting the desired uncomfortable squirm out of him, you let him off the hook. “I live here. My apartment is about 3 miles north of here.”

    Dean pulled out of the parking lot and started driving north. Within ten minutes you had him directed toward your apartment complex and pulling into the driveway to your place. It was more of a townhouse, really. It was entirely too spacious for a single person to live.

    You hopped out of the car and entered the code to the garage door, so dean could pull into the empty stall. You had the same nervous excitement you always had when you were around the man. Even when you were around him all the time, you still had the same feeling, and it was intoxicating. In all your years, he was the only man that had ever gotten that reaction out of you. Gabriel had come close but could never be on the same level as Dean Winchester.

    Following the lead of the locals, you kept a fridge in the garage and while Dean settled Baby for the night, you pulled open the door and pulled out a 12 pack of bottled beer. Dean caught up to you, took the beer and followed you inside.

    “Don’t mind the lack of stuff. I’m hardly ever here. Seemed like a good idea at the time,” you had him put the case on the island counter in the kitchen. Pointedly pausing, you looked at him and waited for his attention. “What’s with the suit?”

    He grinned that wonderful grin of his that made his eyes twinkle and you felt your walls start to come down. You’d tried to put him in a special place in your memories that you only took out for moments when you needed him. The day on the pier was the one you pulled out for your darkest moments.

    “Oh,” Dean said, “I’m ah… still hunting.” He took off his jacket and tie, tossing them on the folding chair you had at your card-table kitchen table. “Needed to talk to the locals today.”

    “Still hunting, huh? Thought for sure you’d be a mechanic or a rock star, or something,” it hurt your heart a little that he was still hunting. When you knew him, he didn’t want to do the “family business,” as he called it. He wanted to get out of it, start a business, raise a family.

    “Yeah, things happened, but, I think things worked out okay,” he explained. “I help people, you know? My life’s had purpose.”

    For a moment, you locked eyes with him. All the regrets, the missed phone calls, the lack of communication, the feelings of abandonment and lost love all passed between you.

    “Dean, I picked up the phone so many times, I even dialed a few times,” you looked at your hands, ashamed of how you had handled things. “I’m sorry, I swear I had a good reason.”

    “Things usually work out how they should,” he tired to sound like he believed it.

    You knew better, unfortunately. “No, this isn’t how things should have been, but I promise, I’ll make it up to you if you let me.”

    There was nothing more than the kitchen island between you, but it may as well have been an ocean. Dean gave you a thoughtful look, grabbed two bottles from the case and handed one to you.

    “How long have you lived here?” he asked, looking around at your sparse furnishings.

    That simple question started the conversation of what they had both been up to over the years. You led Dean around your home and showed him the incredible deck where the two of you settled as you talked.

    “Wait a minute,” he stopped you. “Go back to the bit about Gabriel. How do you know him?”

    You’d been avoiding the conversation for years. You’d had the benefit of time and distance between the two of you for the vast majority, but it was time to let Dean in on why you’d stayed away. Your military work was only one reason, though very important, as to why.

    “Gabriel and I were… close,” you said shyly, trying to gauge his reaction.

    His green eyes went to a dark hazel shade.

    “Go on,” his voice was low.

    You sighed, “I met him around 2006. I liked him a lot, he was fun. We would go party. He was a great person to come home to. With my line of work, it was nice to have someone with whom I could let loose and who wasn’t in the same line of work. Gabe always said he was a lover, not a fighter. I let it slip about my life before him. I didn’t usually do that,” the words wouldn’t stop now. “I told him a lot, maybe too much about you … and Sam. About a year ago, things were getting serious between us and he knew I still had feelings for you, and always would. I swear, Dean, when I found out what he did to you and Sam, I threatened to use an angel blade on him.”

    Dean sat in silence, mulling over what you had told him. In the glow from the inside of the apartment, you could just see his eyebrow was cocked up at you.

    “You know an angel blade wouldn’t kill him, right?” he asked.

    “I didn’t say I would kill him. Told him I would cut off pieces, make him wish he was dead,” you were still mad at the archangel even though he’d been gone for a few years. “I know what Lucifer did, but archangels aren’t ever really dead unless God wants them to stay that way. I have no doubt he’ll be back.”

    Dean didn’t dispute her. He’d seen Gabriel die, he was sure of it. It did make him happy that the feelings on his part hadn’t been one-sided. There hadn’t been many days where he hadn’t thought of her and wondered how she was doing. He could see in her eyes that she had been through a lot, maybe even as much as he had. All he wanted to do was take her in his arms, hold her tight, and tell her that everything would be okay. Even if things weren’t okay, he knew that if they were together, they would be.

    He loved her, more than he’d let on to anyone, even her. Watching her get on that bus, and not chase her, tell her how much he loved her, had been the hardest thing he’d ever had to do. Looking at (Y|N) now, even more beautiful than she had been, he realized that the love had never gone away, it had just lain dormant, waiting for that spark to come back, waiting for **_her_** to come back.

    “You did that for me,” he asked, and quickly added, “and Sam?”

    “He said he loved me, but… whether he did or not, what he did to you was not right. He knew I… he knew I cared for you deeply and that got under his skin. I think he saw you as competition…”

    Dean stepped closer to you, “What do you mean, ‘competition’?”

    Dean had always exuded intense appeal. When you knew him, he had the confidence of a young man. He’d always known he was an attractive man, and nothing had changed, he’d only gotten better looking. Your heart rate was picking up, despite your best efforts to remain calm. There had only ever been one man who could get you going merely by being close, and that was Dean Winchester.

    Clearing your throat, you looked up into his eyes, now mere inches from you, “Well, you see, there was this boy I knew.” When his fingertips grazed your waist and snaked around your back, you couldn’t stop yourself from taking in a sharp breath. “He stole my heart and he never really gave it back.”

    His arm pulled you close to him, so there was no space left between the two of you.

    “It’s been a long time, sweetheart,” he said, his voice thick with emotion. “It hurt like hell to let you go.”

    “It was no picnic for me, either,” you told him, putting your arms around him. “I don’t want to let you go again.”

    “Is there anything, or anyone, keeping you here?” he asked. Judging by the lack of anything that even remotely looked like it belonged to someone other than (Y|N), he barely took a breath waiting for her answer.

    “No, there’s no one. Nothing holding me here,” you told him.

    “No military?” he asked.

    “No military,” you said.

    He gave you a questioning look after that, but you would be happy to tell him everything, as long as he was willing to listen. You could feel his body relax at your answer and a smile touched his lips.

    “Then come back with me. Me and Sammy, we’ve got a place. It’s a little, utilitarian, but it’s a home. It’s our home. It’s got all kinds of cool stuff in it…”

    He would have continued if you hadn’t stopped him, “I swear, if you don’t kiss me soon…”

    Not one to keep a lady waiting, he happily obliged. When his lips met yours, it was like no time had passed between the two of you. You were back on that pier in Santa Monica, having the best time of your life, in love with Dean. The memories of the evenings you spent with him swirled in your brain, warming you further.

    When he finally let you come up for air, you said, “We have a lot of catching up to do.”

    He nodded in agreement, his eyes still closed, breathing deeply. His eyes fluttered open, meeting yours, “Yeah we do. I don’t want to miss another moment with you.”


End file.
